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This story appears in the November 2005 issue of Entrepreneur. Subscribe »

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Bradley Skaggs lost track of his frequent flier mileage balance long ago. But the 38-year-old keeps close tabs on the messenger bag he carries on routine cross-country flights for his eponymous firm, Skaggs. It's loaded with gadgets including his 15-inch G4 Apple PowerBook, his Sony Ericsson P900 mobile phone and, yes, his Apple iPod. The latter, by the way, doubles as a backup drive for his computer. "I could boot off it if I needed to," Skaggs says.

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